The plea bargaining was long and difficult. The defendant, Peter Rollock, the leader of a Bronx narcotics gang, had been charged in seven killings. Federal prosecutors wanted the death penalty; any plea deal would have to include a mandatory life sentence.

But prosecutors had another demand: because Mr. Rollock, then 25, had been accused of ordering some of the killings from jail, he would be placed in solitary confinement and barred from communicating with virtually all outsiders.

Pistol Pete, as Mr. Rollock was known, agreed to the deal, and in late 2000, he was sent to the federal Supermax prison, as the Administrative Maximum, or ADX, facility in Florence, Colo., is known, and where some of the nation’s most infamous criminals are housed. With that, he might have retreated from public view forever.

But Mr. Rollock, now 37, has not retreated. In his nearly 12 years in isolation at the Supermax, he has maintained a spotless record, his lawyers say. He has spent countless hours taking adult education courses through a closed-circuit television in his cell. He has even written a novel, “Trigga,” described by his lawyers as a cautionary tale for young gangsters. His family self-published the book; it is available on Web sites like Amazon.com.

Still, Mr. Rollock’s behavior has not led to the most important change he seeks: relaxing the harsh conditions of his confinement and allowing him to enter the prison’s general population.

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After the sentencing of Peter Rollock (whose name has also been spelled Rollack), the authorities distributed these posters in the Bronx.

Although Mr. Rollock’s deal with the government mandated a review of his status after 18 months, the Bureau of Prisons has consistently refused to ease the restrictions, even though one Supermax supervisor recommended in 2005 that he be placed in the general population.

Federal prosecutors have not wavered in their concerns. To them, Mr. Rollock was a ruthless killer whose gang, Sex, Money and Murder, or S.M.M., terrorized parts of the Bronx and made its presence felt everywhere, “in the shot-out streetlights, the bullet-riddled buildings and the graffiti with which S.M.M. members memorialize their gang on every available wall,” the government has written.

The prosecutors argue that their concern about Mr. Rollock’s ability to communicate with outsiders, or even with fellow prisoners, is well founded. They have said in court, for example, that while Mr. Rollock was jailed in New York before his sentencing in November 2000, he gave an interview to a magazine that is popular in prisons and disclosed the names of former gang members who had cooperated against him; as a result, the government says, it had to place people in the witness protection program.

“Mr. Rollock’s name still has significant cachet on the streets in the Bronx,” a prosecutor at the time, David M. Rody, told a judge in 2010. He said that he had no doubt what would happen if Mr. Rollock decided to place “a hit” on a witness and the message got out to his gang.

“I am not saying he is ordering anything,” Mr. Rody said, “but our concern is that if he did, these people would act on it in a heartbeat.”

Mr. Rollock spends 23 hours a day in his cell at the Supermax, and is allowed one hour for exercise. He receives meals through a slot in his door. He is allowed limited calls.

Mr. Rollock’s story is not that of an innocent man wrongly convicted. When he pleaded guilty in 2000, he admitted in Federal District Court in Manhattan that he had led the violent S.M.M. gang, which had sold crack cocaine and heroin in the Bronx as well as in Pittsburgh and North Carolina.

“We possessed firearms and committed murder,” he told Judge Miriam Goldman Cedarbaum, describing killings he had carried out or approved from jail.

In one 1993 case, he said, he fatally shot a man who had drawn his gun on a fellow gang member. “We protected one another,” Mr. Rollock explained.

In another case, in 1994, he was entering a sneaker store when he saw an associate of another of his recent victims. He fatally shot him, too. “I knew that he was a danger to me,” Mr. Rollock said.

While Mr. Rollock (whose name has also been spelled Rollack) was jailed at Rikers Island around late 1995, a federal indictment charges, he joined the Bloods gang and made S.M.M. a kind of local affiliate.

In 1997, after he was transferred to a jail in Charlotte, N.C., to face narcotics charges there, the authorities have said, he sent a coded letter to his girlfriend that led to the murders of two men during an annual Thanksgiving football game between residents of the Soundview and Castle Hill Houses in the Bronx. One victim was thought to be cooperating with the government.

Mr. Rollock was later returned to New York to face the charges that carried the death penalty; at some point, the authorities restricted his ability to communicate from jail, even with his father, Leonard Rollock, who was serving a long sentence in a federal prison elsewhere. “We have concerns that he may enlist his father to have his father’s associates do harm to the witnesses and/or their families,” a prosecutor wrote then.

Around the time of Peter Rollock’s sentencing, the authorities distributed posters in the Bronx that included his photograph and the words “Life without parole.”

The Supermax houses more than 400 of what the Bureau of Prisons calls its most violent and escape-prone inmates. These include Ramzi Ahmed Yousef, who led the first World Trade Center attack; Theodore Kaczynski, the Unabomber; and Umar Farouk Abdulmutallab, the so-called underwear bomber. Timothy J. McVeigh, the Oklahoma City bomber, was held there before being executed in 2001 in Terre Haute, Ind.

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The typical cell is 7 ½ feet by 10 feet. In cases where the attorney general finds that allowing a prisoner to communicate with others could result in “death or serious bodily injury,” the Bureau of Prisons imposes special administrative measures, or S.A.M.’s, limiting access to mail, calls and visitors, but at least leaving open the possibility of an inmate’s “stepping down,” that is someday earning an easing of restrictions. But in Mr. Rollock’s case, restrictions were imposed as part of the sentence itself, and he claims he was told he would never be allowed into the “step-down” program.

Prosecutors agreed last year to modify his deal, and have Mr. Rollock placed under S.A.M.’s instead, but his lawyers argue that his ability to earn his way out of solitary confinement could still take years to accomplish, if it ever occurred.

Mr. Rollock, after arriving at the Supermax in December 2000, threw himself into education, beginning his path toward redemption, his lawyers say. By the end of 2002, he had taken closed-circuit television courses in philosophy, political theory and economics, and he had earned his G.E.D., records show.

Reviews of his status were conducted, but prison officials found him not suitable to be moved in order “to prevent his contact with cooperating witnesses or former gang members,” as one memo said.

In 2006, Mr. Rollock appealed to prison officials: “I have clearly surpassed all program participation requirements and have maintained clear conduct for six years,” he wrote. He said he wanted to “begin the process of working my way out” of the Supermax and into a regular prison. The appeal was unsuccessful.

Meanwhile, he was also writing. In 2006, with the help of family members, his 150-page novel, “Trigga,” was published by a print-on-demand company in Alabama. In addition to several early bulk orders, the company said recently, the book had sold 116 copies through Amazon and other outlets. The cover says the book is written by “Team Rollock,” but his lawyers say Mr. Rollock was the author.

“Peter wrote the book ‘Trigga’ in longhand,” said Kevin M. McNally, another of Mr. Rollock’s lawyers. “It is indeed a cautionary tale for young gang members. Peter meant it to be.”

Supermax officials read the manuscript and allowed it to be sent to family members on his approved list, Mr. McNally said. After the book was published, he added, the prison refused to allow Mr. Rollock to receive a copy.

Prosecutors have made it clear that they believe the book glorifies Mr. Rollock’s criminal exploits.

But Mr. Moskowitz, Mr. Rollock’s lawyer, countered that the book was a work of fiction, and had left the Supermax with full approval. “They knew about it, they read it, they let it out,” he said in court.

The Bureau of Prisons and prosecutors refused to comment on Mr. Rollock’s case or the book.

The cover features a photograph of a gun. The novel, written raw, features a character named Tyvon and a drug gang called Money & Murder. The novel ends with Tyvon’s being shot; as he dies, he realizes that he has dedicated his life to the street, trying to increase his “money stacks.”

“But what did I accomplish?” he asks. “If all fast money does is hurt, can someone please explain what is its worth? The average street kid wont’ makes it out of his 20s before he is place in the dirt.”

By the end of 2006, Mr. Rollock had accumulated more than 1,400 hours of closed-circuit television courses, including Classical Mythology, the Joy of Science and History of Ancient Rome; he had also viewed a program in anger management.

“Other prisoners at ADX have gone insane under such conditions,” Mr. McNally said. “Peter has not. He continues to educate himself every day. He takes advantage of exercise when available.”

Nonetheless, prosecutors remained strongly opposed to easing the conditions of Mr. Rollock’s confinement; they have noted that his reputation from the street endures. In recent years, they say, “Pistol Pete” graffiti has been found in the Bronx, and during arrests and searches of Bloods members who had nothing to do with S.M.M., authorities have uncovered “Bloods literature and materials which talk all about Peter Rollock,” Mr. Rody, the prosecutor, told Judge Cedarbaum in 2010.

If Mr. Rollock were allowed to mix with other prisoners, he could pass messages through inmates who were not subject to communications restrictions, Mr. Rody said, adding, “He knows who cooperated against him and the rest of his organization.”

A current prosecutor, Margaret M. Garnett, said last year in court that Mr. Rollock and his family had been discussing a business called Team Rollock, which would “monetize and capitalize” on his reputation on the street. She even cited talk of Team Rollock T-shirts, with a rifle sight as the “primary design element.”

As for Mr. Rollock, his book seems to address the possibility his status may never change. “Freedom, prison or death,” Tyvon ruminates. “The two negatives were stacked up against the positive. But that was the life he chose. Of course he didn’t want to die or go to prison,” he added. “But he was prepared for it if it came to that.”

A version of this article appears in print on July 9, 2012, on Page A13 of the New York edition with the headline: Pondering Solitary Future for Gangster Held in Isolation for Years. Order Reprints|Today's Paper|Subscribe